Overview Nantucket Race Week is a stretch of August sailing on Nantucket Harbor and Nantucket Sound that closes on the Opera House Cup, a classic-yacht race first sailed in 1973 in which early 20th-century Herreshoff designs line up against modern boats by Botin and Frers. Between the youth Opti and 420 regattas at the start and the Cup at the end come one-design fleets, a Women's Regatta, kiteboarding and winging, a Harbor Race, the big-boat Nantucket Regatta and a Celebrity Invitational. The Nantucket Yacht Club and the Great Harbor Yacht Club host, and the organizers' 2026 sponsorship page says the week raises about a quarter of Nantucket Community Sailing's annual operating budget. NCS is a US Sailing-accredited community sailing center and licensed children's camp on the island. On site The two courses sail differently: the harbor has tricky currents and shifting sandbars, and the Sound has deep water and a steady sea breeze, with Great Point Lighthouse on the Cup course. Cup weekend opens with a Classic Yacht Exhibition on Saturday evening and a Parade of Yachts past Brant Point on Sunday morning before the start, and the awards party runs that night on Jetties Beach. Around the racing run Brewery Night, the NCS Gala and the Rocks and Royals exhibition. In 2026 the Cup added an Invitational Division for non-wooden hulls, sailing for a new Lighthouse Trophy. Audience Race Week counts about 3,000 participants and nearly 300 boats, so most of the crowd is on the water or crewing for someone who is, from junior sailors in single-handed Optis to owners of classic wooden yachts. Individual supporters give at levels the organizers name Ensign, Captain, Commodore, Rear Admiral, Admiral and Secretary of the Navy. Talent and Influencers The Celebrity Invitational puts four-person amateur crews in identical International One Designs, assigned by draw, each with an Olympic medalist, America's Cup sailor or world champion aboard as tactician. Teams can bid for the tactician they want in a sealed-bid auction. Dawn Riley was master of ceremonies for the 21st edition in 2026. Track record The Opera House Cup began at the Opera House Restaurant on South Water Street, where owner Gwen Gaillard, manager Chick Walsh and local sailors Dick Deutsch and Tony Topping drew up the first courses and rules with the skippers. It is scored under the CRF rating system as part of the CYOA Classic Yacht Series. Peter Cassidy's 45-foot sloop Siren won the 53rd Cup in 2025 in heavy wind. Brand presence The title partner's name goes on both Nantucket Race Week and the Opera House Cup. Below it, partners can take naming rights on individual regattas, attach to the social events, present awards and run activations on the water, with logos on the website and race documents and ads in the Race Week and Opera House Cup program. The organizers listed more than 30 corporate and local business partners in 2026.